Unlikely Couple
by boqlover
Summary: After the 'Kiss on the Lips' party Chuck and Blair plan their revenge... among other things. As expected scandal ensues.
1. My Night

Jenny sat sandwiched between her brother and Serena. She would have been in more awe if she hadn't been shaking so hard. It figured that at her first big party she would get attacked by that sleaze ball Chuck. She had read lots of stories about him on Gossip Girl but somehow when he started talking to her she had forgotten it all. She'd forgotten everything.

"Are you alright." said Dan, holding onto her shoulder.

"Yeah you have to watch out for Chuck." said Serena holding onto one of Jenny's hands.

"I'm fine." said Jenny squeezing Serena's hand. "Thank you, I'm so sorry ruined your date."

"There's always more." Said Serena leaning over Jenny to look at Dan. Despite her shaky position she looked at Dan pointedly. How was it that on the night was supposed to be the greatest of her life gone so wrong and her pathetic excuse for a man brother had landed a date with Serena van der Woodsen.

* * *

Blair stood next to Chuck glaring at the back of the taxi carrying Serena. Somehow she had managed to waltz into her party for five minutes and steal the spotlight. Blair saw the writing on the wall and serena was he headline. "We need to get things back to the way they were. She can't-"

"I'm fully aware of what needs to be done. The question is how to bring her down and get that Jenny girl back."

"Eww! Obsession much? She's a freshman for gods' sake. And you could do better."

"Like you Blair?"Said Chuck smiling suggestively.

"In your dreams." said Blair walking back to the party.

"How did you know?"Said Chuck following her inside.

* * *

"Do you have any ideas on how to do it.?" Said Chuck sitting on the edge of his bed on his forest green comforter.

"Actually… I have several." Said Blair sitting across from him on his mahogany desk smoothing her brown silk Ella Moss shirt.

"Any that includes me finally getting with Jenny?"

"Are you serious? I thought you were kidding."said Blair her nose wrinkling. She tapped her buffed nails on his desk. She leaned against his wall and closed her eyes sighing heavily.

"What's wrong B?"Chuck said rubbing her bare arms. Blair leaned forward and rested her head on Chucks' cashmere covered shoulder.

"What's going to happen to me?" whined Blair.

"What do you mean?" said Chuck smoothing out the kinks in her hair and turning around a bent curl.

"I mean with Serena. As soon as she left I was the one on top-" Chuck opened his mouth. "Don't say it." she said rolling her eyes.

"Sorry I have to it's to perfect-" said Chuck half laughing.

"I got everything she had when she left and Nate and I were happy. And now she's back and … I just don't know what's going to happen to me- us." She hugged Chucks neck burying her face in his cologne-scented shoulder. He hugged her back then began kissing her neck. "Chuck, stop it." She said pushing him away. He held onto her waist and kissed her again. "What is wrong with you?"

"You know this is meant to be. We had that spring break in Cancuun…"

"That was two years ago! And it was just one night. I'm with Nate remember him, your best friend? Since kindergarden?" she held him at arms length.

"Oh like you didn't want it? "

"What would give you that idea?"

"Oh I don't know the fact that you are sitting in my room, alone. And you came to me before your boyfriend." he said leaning into her ear and stroking the side of her neck and face. Blair looked away but didn't stop when Chuck kissed her again, this time more involved. When he kissed her neck again she said, without much conviction, "How can I be mad at Nate for being unfaithful,when I can't even be-"

"Shhh."said Chuck and resumed kissing Blair. She sat back as Chuck slid his hand up her back.

* * *

"So how's this for a second date?"said Serena scooping up the last drips of ice cream from her bowl. Dan leaned back in his chair looking at her. "What?" said Serena tilting her head to the side.

"Nothing."said Dan snapping out of his stupor. "I was just thinking."

"How's Jenny doing?"said Serena.

"Fine she just took dad's credit card to Bendell's and $200 later she was fine."

"I could take her shopping one of these days. I've got a membership at almost every store in the city."

"I think she'd like that." said Dan smiling. "How is it being back again."

"It's great ." said Serena a strained smile stretching across her face. "Just hard catching up with everything going on. Do you know who won fall debutante this year?"

"Not really. I don't follow in debutante circles."

"Oh."she said recognizing his uncomfortable expression. "What have you been up to?"

"Not much I've just been writing and visiting my Mom."

"When did you see her last?"

"Actually not long ago, I came back from her place last week."

"Really when did you get home?"

" Saturday afternoon."

"Really? Where were you?"

"Grand Central Station."

"Really that's where I got home on Saturday."

"I know I saw you there, you walked right by me and Jenny."

"Why didn't you two say anything?"said Serena sitting up.

"You didn't really know us." Said Dan looking down,

"I'm glad I do now." Said Serena smiling.


	2. Really?

Chuck sat fuming on the edge of his bed rebuttoning his shirt. He ran his hand through his highlighted hair.

"What, you really thought I would give it up that easily? I've made Nate wait this long. I thought it was understood we were just messing around." Blair held onto his shoulder her barely clad chest pushing against his back. He shrugged her hand off ,straightened his collar and stood up. Blair fell forward and looked at Chuck puzzled. "What? Come on can you imagine what would happen if we slept together? You saw what it did to me and Serena. And what happened to Serena? You would lose Nate as a friend and your complete social status."

"What are we going to do about Serena?"said Chuck shortly. "and how can I land Jenny? Fast?" his familiar mischievous smile returned.

"Umm actually they're kind of are the same thing." said Blair tying her shirt back up.

* * *

As Jenny's scuffed three year old cell phone rang she rolled over groggily wiping her smeared eyeliner. "Hello?"she said her voice thick with sleepy phlegm.

"Is this Jenny Humphrey?"said a familiar voice.

"Yes, this is Jenny. Who is this?" she said not really believing it was-

"This is Blair Waldorf. You made my invitations for Kiss on the Lips?"

"Oh of course Blair, this is Jenny." Stupid, she thought, you already said that. "Um, Hi Blair, what uh- How are you?"

"Fine, how are you?" Jenny waited to hear why Blair had really called her. Did she have another batch of 500 invitations she needed made? "Jenny? Hello, are you there?"

"Yeah- I mean yes. I was just- Why are you calling me?"Jenny flinched at her bluntness.

"Just to see if you'd like to join me at a sample sale at Bergdorf's today. At about 4? They got a new line in and some of the colors were just made for you!"

"Sure, should I just meet you there or-"

"No, I'll pick you up in my town car at 3:45. Sound good?"

"That sounds really really great. To bad I can't buy much more. I borrowed my Dad's credit card yesterday to go shopping and he went crazy."

"Oh don't worry about it, my treat. See you soon!" Jenny clicked of her phone and threw it back to her nightstand. She picked it back up and stared at the screen to make sure Blair Waldorf had really just called her and last nights events had not caused an early morining hallutionation.

* * *

"What about this one?" said Jenny holding up a forest green silky shirt.

"I think it would look better in black." said Blair holding up her preference.

''Blair? Is Chuck- Because I didn't do anything and-" said Jenny sifting through piles of clothes.

"You should really give Chuck a second chance." said Blair considering a pair of knee high black boots by Prada "I know he can come off as kind of a jerk but he can really be a great guy if you get to know him."

"I don't mean to say you're lying or anything but Chuck, he just scares me. I don't think I could give him a second chance." said Jenny following Blair to the next department."

"He actually did talk to me about you. He knows that what he did really made you uncomfortable-"

"He attacked me on a rooftop and it took my brother burying his fist in his face to get him off me. I am beyond uncomfortable. I know he's your friend and all but-"

"Listen, Chuck is a guy who goes for what he wants and doesn't think about what he's done until its too late. I think he genuinely…" Blair handed her personal shopper Jenny's top. "admires you."

* * *

"So how did it go?"said Chuck as Blair stepped off the elevator into her lobby." Has Little miss freshman pledged herself to me yet?" he fingered his newly dry-cleaned scarf around his neck. 


	3. Sounds Promising

"Hardly,"said Blair breezing by him with her dozen or so shopping bags. "These things take time to work. But I did get her to stop flinching whenever I mentioned your name." she shoved her bags to the floor and she began digging around her oversized bag for her keys. Chuck pulled a spare from his back pocket and opened the door for her. "It doesn't even surprise me that you have a key to my place." Blair scooped up her bags and dumped them on her bed. "Ugh, today was excruciating."

"Oh poor little rich girl had to go shopping all day! Let's all shed a tear for Blair in the part of poor suffering girl." Said Chuck swooning mockingly onto her bed.

"You have obviously never had to take a girl shopping who thinks forrest green is in her color palate when she's clearly a winter." Blair pulled a deep red halter from a signature orange bag. "Do you think this makes me look fat?"said Blair holding it over her.

"Blair, shut up, you are as skinny as humanly possible. A fat suit couldn't make you look fat."

"Thank you Chuck, for your insulting compliment. And as the answer to your previous question, I have managed to set up time for you to meet her today."

"Sounds promising." he said sitting up, his interest peaked.

"In about," Blair looked at her Rolex. "Ten minutes Jenny is coming over to help me sort rejects out of my closet into hers. Unfortunatley I will have forgotten that I was supposed to meet Nate for coffee but she's welcome to stay with you. What you do with her I don't care to know."

"Blair you are a devious, underhanded. plotting Upper East Side rich witch. I am proud to be your friend." Said Chuck placing his hand mockingly over his heart.

* * *

Jenny knocked on Blair's front door tentaivly wobbling in the kitten heels Blair assured her would stretch her legs to model proportions. Blair trotted down the stairs in tight darkwash jeans and a pearl colored cashmere turtleneck. "Hello Jennifer, I am so sorry about this."

"About what?"said Jenny her doe-like chocolate eyes widening.

"Well Nate and I had plans to have coffee and I completely forgot."

"Oh well I'll leave then, sorry to-"

"You dragged yourself all the way to my place and I've got a friend up in my room who can help you get my stuff to your place."

"Who's in you room-"

"Bye Jennifer!" said Blair breezing by her. Jenny watched Blair leave, then looked up her stairs then started towards her room.


	4. Why Should I

"Hello?" said Jenny peering through Blair's' door. She saw a flash of red, white and black silk.

"Jennifer?" said Chuck rising from Blair's' bed and turning towards Jenny.

"Chuck I didn't know- I should leave- Blair didn't-"Jenny backed up into a closet door fumbling in her purse for her cell phone.

"Jennifer, Jennifer, Jenny." Said Chuck taking a step forward every time he said her name. "Calm down." he said pushing her hair out of her face as he seemingly accidently backed her into a corner. Jenny stood shaking underneath his hands. "You don't have to worry about me."

"Yes I do!" said Jenny ducking under his arm backing into the bedroom door fumbling for the doorknob. "I need out of- You are-"

"Jenny look," said Chuck putting his hands up to clearly show he was keeping his hands off. "I'm sorry about what happened at Kiss on the Lips. You were- are so beautiful and I couldn't stop myself on the roof,"

"It's not like that's the first time you've pulled that kind of thing." Said Jenny standing a little taller. "I know what kind of person you're like, and I need to get away from you."

"Jennifer, can I just talk to you for five minutes. That's all I want to do, talk."

"Why should I?"

"What do you have to lose?"

"Five minutes, that's it and I'm gone."

* * *

"Mom! Where's my black Coach bag!" said Serena digging through cardboard boxes.

"No, Serena I have not seen your bag and where are you going anyway?"

"Just to see Eric." Said Serena avoiding eye contact with her mother

"Why do you keep sleeping over there, rather than you own bed."

"Because, apparently, I'm the only one who actually cares about him. In this family." Said Serena pulling her black bag out from under her pillow.

"That's not true."said her mother angrily. "You know that full well-"

"Does Eric?" said Serena stopping for a moment before turning on the heel of her scuffed, silver flats.

* * *

"So I'm sorry." Said Chuck holding Jenny to his chest. She leaned into him breathing in the sweet smell of his cologne, her face rubbing against his scarf. She pulled away from his

hug and leaned back against the wall behind Blair's' bed.

"Maybe I did misjudge you Chuck. " said Jenny leaning on his shoulder again. "You seem really amazing." Her soft brown eyes met with his sharp hazel ones. He leaned

forward and his fingertips brushed her cheekbone than pulled her face to his. Their lips met and his mouth engulfed hers. This time she leaned back into him. His hands held her

sides firmly as he rolled onto his back pulling Jenny on top of him his hands sliding up the back of her shirt. She squeaked then flinched. Had she really just squeaked in front of

Chuck Bass? Above Chuck Bass actually. His hands continued rubbing up her back his kisses spreading down her neck. He rolled over pining Jenny under him. She gasped then

pushed against him. "Chuck stop it." She said struggling to get out from under him. He held her hands down on the mattress.

"I finally got you where I want you Jenny."said Chuck leaning into her ear. "I have to admit you were a bit more challenging than most." Jenny struggled violently under him using

all her strength her heart racing. She only managed to free her arms for a few seconds before Chuck pinned them to the wall.


	5. Didn't you

Chuck pushed Jenny harder into the wall. She tried to scream but Chuck pushed his tongue into her mouth stifling her attempt at a scream. He pulled at her shirt, ripping through

the zipper. "Stop, please." Said Jenny pulling away from him long enough to whisper her plea.

"Jenny look." said Chuck pinning her down with his legs, running his hand through his hair. "You may not believe me but this is the way to get into this world. I am your ticket to

big parties, new clothes and amazing friends. You may not admit it but you wanted this."

"No I didn't," said Jenny lying still for a few seconds. "I didn't even know you were here."

"But you did want to be part of this." Said Chuck pulling another kiss from her lips. She closed her eyes and turned her head but didn't push against him this time. He fell back

into her and tangled his fingers in her hair. He saw her eyes open and looked blankly at the ceiling. He pulled at her waistband working her wide, leather belt buckle loose. She

didn't fight back just kept staring at the wall. "So Jen-"

"Shut up." said Jenny and pulled Chuck's mouth to hers. He looked at her surprised, and then pulled her skirt off. She wrapped her hands around his neck then rolled onto her

side. His hands slid up her thighs to her tiny waist. She pulled her stomach in as his strong hands gripped her sides and his nails dug into her. He rolled back on top of her then

leaned over to flip the lights off.

* * *

"Nate…"whined Blair, "why can't you go out tomorrow. I had a whole day planned out."

"I told you," he said "my dad scheduled a Dartmouth interview tomorrow and he'll give me hell if I don't go."

"But you know I would have made it worth your while." said Blair running her fingers over Nate's thin, cotton shirt. She felt him tense up under her French-manicured nails. He grabbed her hand and moved it up to his smooth face.

"Blair I'm sorry, but my future is on the line. I promise as soon as the interview is over we can do something together."

"Not just something." said Blair leaning into Nate. "It."

* * *

Jenny sat next to Chuck, his arms folded comfortably behind his head. Jenny she held Blair's 800 count sheets over her bare feet. Her rumpled skirt and ripped top were

wrapped around her. She looked over at Chuck and he looked at her dripping with charm. Jenny, despite her shocked condition, melted and she wrapped her arm across Chuck

her small hands resting on his bare lacrosse toned shoulders. He looked at her then ran his fingers across her arm. "We should probably get out of Blair's bed." he said sitting up

and rolling out of bed.

"Don't you have a suite waiting for you?" said Jenny coyly her post-hookup hair falling in her face one leg hanging off the side of the bed.

"Feisty, aren't you?" Chuck buttoned up his white shirt then tied his signature scarf around his neck. She fingered it, then kissed Chuck, her arms around his neck.


	6. Much Better

Jenny stretched across Chuck's bed in her sleep tucking her hand under her chin the linen of his shirt scratching her neck. He grabbed her around the waist and rolled over her pinning her wrists to the bed. She sleepily opened her eyes then fought against him without much real conviction. He pushed her arms above her head licking the side of her neck roughly his intentions clear. "Chuck," said Jenny, her hands sliding from underneath his slackened grip, "How are you not exhausted?"

"I was built for stamina."he said pushing her hands back against the wall.

"I can barely keep my eyes open." She curled into a ball pulling his shirt around her.

"Come on Jennifer I need you." He said biting his lip as he ground his hips into her. She closed her eyes momentarily then sat up. "That's better now let's-"

"Chuck in case you've forgotten we have school in forty-five minutes."said Jenny rolling out of bed.

"You are picking school over me. Really? We can just cut class and stay here."

"That sounds tempting, but-" said Jenny turning around to take off Chuck's shirt and change into her own uniform. "I can't. My dad-"

"Won't let you cut school but will let you disappear off into a boys room for hours on end alone?"

"I'm not telling him about you." said Jenny turning around to face Chuck as she zipped up her skirt. "He thinks I'm studying or shopping with Blair."

"And he believes you?" said Chuck tying his shoes then straightening his tie.

"I've never given him a reason not to." Said Jenny looking almost regretful. She pulled her hair out of her face and into a messy bun secured with a decrative chopstick she'd bought years ago.

"Your hair looks better down." said Chuck unchararteristically. "Makes me remeber what a sexy girl you are." His familiar smile flashed across his face before engulfing Jenny's mouth. She leaned back as Chuck leaned against her pulling the black and gold chopstick from her hair. He pulled back and ran his fingers through her hair. "Much better."

"Who knew?" said Jenny walking down the hotel's hallway by Chuck's side. "Chuck Bass: Bad Rich Boy and personal stylist."

"Say anything to anyone and the next hairstyle you'll be sporting is Britney in rehab bald."

"Now how would you manage that? I am a noutorious light sleeper." said Jenny climbing into the back of Chuck's towncar.

"Easy," he said climbing in after her and closing the door. "I'm Chuck Bass."

"Is that your answer to everything?"

"It hasn't been wrong yet." he said his hand sliding non-chalantly across the control panel. "Now lets make the fifteen minutes to school worthwhile." he pushed down on the button that rose the partition between him and the driver.


	7. Done with Her

"I'm bored with her." said Chuck staring at Blair's ceiling. "The cute innocent thing only works for so long before it becomes annoying."

"Wow, a whole, what is it, week since I had to boil, bleach and ultimatley burn my sheets because of you, and you're done?" said Blair holding a slinky silver skirt across her hips. "What do you think?" she said turnng to Chuck for approval.

"Don't walk down any streets without setting your price first." he said rolling his eyes. "How did this have anything to do with us ruining Serena?"

"Well," said Blair picking up a burgundy pair of suede boots, "In case you haven't notticed little Jenny is quite obssesed with becoming one of us. That means going to whatever

girl she thinks can get her there faster."

"Yes and?" said Chuck. "Her being your new best friend/ personal assistant isn't exactly news."

"Well what's news is the dirt I've been able to get from her. She's such a nobody no one recognizes when she's where she shouldn't be."

"Freshman." said Chuck sitting up "They're the only way to get through this life without serious drugs. So what has she been able to dig up?"

* * *

Serena sat in front of the TV mindlessly watching America's Next Top Model her chin resting on her knees. When she heard the card reader beep and the door open she

assumed her mother was back from shopping. Shhe looked over her shoulder to say hello but was, needless to say, shocked to see Chuck standing behind her.


	8. Better Not

"Hello Serena." He said sliding the master key card into his pocket. "How are you and Brooklyn Boy doing?"

"What are you doing here?" said Serena turning off the TV standing up to glare at him. "Chuck you may own this hotel but get out."

"Nice to see you to S." he said rolling his eyes and stepping closer to her."No welcome back-"

"I've hit you once and I'll do it again." Said Serena wishing she had put on shoes before going straight to the couch that morning.

"Why must you always be on the defense? I just came to talk to you." Said Chuck settling into the large armchair next to the couch, "Not like you need much of an invitation to wrap your legs around a guy these days."

"I told you," said Serena "sitting tentatively on the opposite arm of the couch," I'm changing. Or trying to…"

"But it's hard to change when your best friend's boyfriend loves you instead of her. Isn't it?" Said Chuck sitting back in the chair enjoying Serena trying to hide the combined look of hurt, and surprise on her face.

"What are you talking about?" she said standing up and turning around and busying herself by rummaging through one of the unpacked boxes.

"Oh come on Serena everyone saw his face when you showed up at Blair's." he said standing behind her. "Even if I hadn't seen the two of riding each other at the Sheppard wedding I would have known something had happened." Serena turned around to respond but Chuck caught her wrists and glared at her. "Don't try it S you know what I can do." A look a fear flashed through her eyes before he let go of her. "Just remember I know everything the next time you feel like hitting me or insulting me in a public manner again." He said walking out the door. "Or Gossip Girl will be getting some interesting new information."

Blair sat impatiently tapping her black Jimmy Choo pumps on the steps of Constance Billiards' main building. Nate rounded the corner out of breath his hair deliciously mussed. "Hey." she said wrapping her hands around his shoulders. He wrapped his hands around her waist rubbing against the buttery softness of her sweater. She kissed him slowly but he pulled away almost as soon as their lips touched. "What is it?" she said leaning back to examine his bright green eyes.

"Nothing." He said looking away distractedly.

"Good," she said pulling a section of hair out of his eyes. "Because I thought we could go for sushi tonight and then maybe…" she said pulling softly on his tie, "We could go back to my place for dessert. My mom's in Paris for three days and its lonely all by myself." She looked back at him biting her lip but he was still looking away. "Nate?"

"Yeah." He said snapping out of his thoughts looking into Blair's' eyes. "Sushi sounds great." Blair wrapped her fingers around his and he walked next to her still not listening to a word she was saying. He saw Serena talking to someone and he almost called out but then saw she was talking to Dan and turned back to Blair.


End file.
